Synthesis and Transformation of Glycosyl Azides

Z. Györgydeák, Joachim Thiem

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

Owing to their functional group, glycosyl azides (general structure Glyc-N3) constitute important and versatile derivatives for carbohydrate chemistry. Because of the dipole character of organic azides (see resonance structures A, B, and C) they can function both as nucleophiles and electrophiles, and readily undergo dipolar cycloadditions. Further, as configurationally stable groups, azides are well suited as starting materials for formation of other nitrogen-containing functionalities, such as amines, amides, ureas, carbodiimides, and others.{A figure is presented}. The current article ties in with previous ones that were published in 19611 and 1993.2 In the past decade there have been reports on a number of relevant preparative approaches and uses of anomeric glycosyl azides, which provide a plethora of synthetic options for carbohydrate chemistry.

Original languageEnglish
Pages (from-to)103-182
Number of pages80
JournalAdvances in Carbohydrate Chemistry and Biochemistry
Volume60
DOIs
Publication statusPublished - 2006

Fingerprint

Azides
Carbohydrates
Carbodiimides
Nucleophiles
Cycloaddition
Cycloaddition Reaction
Amides
Functional groups
Amines
Urea
Nitrogen
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Synthesis and Transformation of Glycosyl Azides. / Györgydeák, Z.; Thiem, Joachim.

In: Advances in Carbohydrate Chemistry and Biochemistry, Vol. 60, 2006, p. 103-182.

Research output: Contribution to journalArticle

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